Syntheses and structures of novel heteroarene-fused coplanar π-conjugated chromophores

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5033-5036

  Wong, Ken Tsung ^a   Chao, Teng Chih ^a   Chi, Liang Chen ^a   Chu, Ying Ying ^a   Balaiah, Akula ^a   Chiu, Shih Feng ^a   Liu, Yi Hung ^a   Wang, Yu ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750918298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061791y     Document Type: Article

References (30)

1. (a) Scherf, U. J. Mater. Chem. 1999, 9, 1853.
2. (b) Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592.
3. (a) Setayesh, S.; Marsitzky, D.; Müllen, K. Macromolecules 2000, 33, 2016.
4. (b) Jacob, J.; Zhang, J.; Grimsdale, A. C.; Müllen, K.; Gaal, M.; List, E. J. W. Macromolecules 2003, 36, 8240.
5. Hertel, D.; Scherf, U.; Bässeler, H. Adv. Mater. 1998, 10, 1119.
6. Yamaguchi, S.; Xu, C.; Tamao, K. J. Am. Chem. Soc. 2003, 125, 13662.
7. (a) Kudoh, K.; Okamoto, T.; Yamaguchi, S. Organometallics 2006, 25, 2374.
8. (b) Wang, C.-H.; Hu, R.-R.; Liang, S.; Chen, J.-H.; Yang, Z.; Pei, J. Tetrahedron Lett. 2005, 46, 8153.
9. (c) Sirringhaus, H.; Friend, R. H.; Wang, C.; Leuninger, J.; Müllen, K. J. Mater. Chem. 1999, 9, 2095.
10. (d) Ahmed, M.; Ashby, J.; Ayad, M.; Meth-Cohn, O. J. Chem. Soc., Perkin Trans, 1 1973, 1099.
11. Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2005, 7, 5301.
12. Agou, T.; Kogayashi, J.; Kawashima, T. Org. Lett. 2006, ASAP.
13. (a) Wakim, S.; Bouchard, J.; Blouim, N.; Michaud, A.; Leclerc M. Org. Lett. 2004, 6, 3413.
14. (b) Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.-Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2051.
15. Wong, K.-T.; Hwu, T-Y.; Balaiah, A.; Chao, T-C.; Fanf, F.-C.; Lee, C.-T.; Peng, Y.-C. Org. Lett. 2006, 8, 1415.
16. Crystal packing diagrams and the analyses of possible intermolecular interactions of molecules 3c, 5, 7, 9, and 15 are provided in the Supporting Information.
17. A polymer related to this structure has been reported previously. Forster, M.; Annan, K. O.; Scherf, U. Macromolecules 1999, 32, 3159.
18. (a) Xu, C.; Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638.
19. (b) Yamaguchi, S.; Xu, C.; Yamada, H.; Wakamiya, A. J. Organomet. Chem. 2005, 690, 5365.
20. Avilov, I.; Marsal, P.; Brédas, J.-L.; Beljonne, D. Adv. Mater. 2004, 16, 1624.
21. (a) Brunner, K.; van Dijken, A.; Borner, H.; Bastiaansen, J. J. A. M.; Kiggen, N. M. M.; Langeveld, B. M. W. J. Am. Chem. Soc. 2004, 126, 6035.
22. (b) van Dijken, A.; Bastiaansen, J. J. A. M.; Kiggen, N. M. M.; Langeveld, B. M. W.; Rothe, C.; Monkman, A.; Bach, I.; Stössel, P.; Brunner, K. J. Am. Chem. Soc. 2004, 126, 7718.
23. The coplanar molecules 5 and 9 may serve as useful core structures for developing potential π-conjugated oligomers or polymers because halogenations can be performed readily at the C2 positions of terminal thiophene moieties. We are currently investigating such reactions.
24. (a) Tsai, M.-H.; Lin, H.-W.; Su, H.-C.; Wu, C.-c.; Fang, F.-C.; Liao, Y.-L.; Wong, K.-T.; Wu, C.-I. Adv. Mater. 2006, 18, 1216.
25. (b) Yeh, S.-J.; Wu, M.-F.; Chen, C.-T.; Song, Y.-H.; Chi, Y.; Ho, M.-H.; Hsu, S.-F.; Chen, C.-H. Adv. Mater. 2005, 17, 285.
26. (c) Tokito, S.; Iijima, T.; Suzuri, Y.; Kita, H.; Tsuzuki, T.; Sato, F. Appl. Phys. Lett. 2003, 83, 569.
27. (d) Holmes, R. J.; Forrest, S. R.; Tung, Y.-J.; Kwong, R. C.; Brown, J. J.; Garon, S.; Thompson, M. E. Appl. Phys. Lett. 2003, 82, 2422 .
28. (a) Qin, S.; Liu, L.; Wang, B.; Shen, F.; Zhang, W.; Li, M.; Ma, Y. Macromolecules 2005, 38, 6782.
29. (b) Patil, S. A.; Scherf, U.; Kadashchuk, A. Adv. Funct. Mater. 2003, 13, 609.
30. (c) Mishra, A. K.; Graf, M.; Grasse, F.; Josemon, J.; List, E. J. W.; Müllen, K. Chem. Mater. 2006, 18, 2879.